Pseudoephedrine
Title: Pseudoephedrine
CAS Registry Number: 90-82-4
CAS Name: (aS)-a-[(1S)-1-(methylamino)ethyl]benzenemethanol
Additional Names: (1S,2S)-2-methylamino-1-phenylpropan-1-ol; d-y-ephedrine; d-isoephedrine
Molecular Formula: C10H15NO
Molecular Weight: 165.23
Percent Composition: C 72.69%, H 9.15%, N 8.48%, O 9.68%
Literature References: Sympathomimetic amine found in plants of the genus Ephedra (Ephedraceae) known in traditional medicine as Ma Huang. a-Adrenergic agonist; (+)-threo-isomer of ephedrine, q.v. Isoln from E. vulgaris: A. Ladenburg, C. Oelschlägel, Ber. 22, 1823 (1889). Synthesis: E. Späth, R. Göhring, Monatsh. Chem. 41, 319 (1920). HPLC determn in Ma Huang: B. J. Gurley et al., J. Pharm. Sci. 87, 1547 (1998); in plasma: P. Guo et al., Biomed. Chromatogr. 13, 61 (1999). Toxicity: M. D. Fairchild, G. A. Alles, J. Pharmacol. Exp. Ther. 158, 135 (1967). Comprehensive description: S. A. Benezra, J. W. McRae, Anal. Profiles Drug Subs. 8, 489-507 (1979). Review of clinical pharmacology: D. T. D. Hughes et al., J. Clin. Hosp. Pharm. 8, 315-321 (1983). Clinical trial for prevention of otic barotrauma: J. S. Jones et al., Am. J. Emerg. Med. 16, 262 (1998); in nasal congestion: D. Taverner et al., Clin. Otolaryngol. 24, 47 (1999).
Properties: Crystals from ether, mp 118-118.7°. [a]D20 +51.2° (in ethanol). Sparingly sol in water. Freely sol in alc or ether.
Melting point: mp 118-118.7°
Optical Rotation: [a]D20 +51.2° (in ethanol)
 
Derivative Type: Hydrochloride
CAS Registry Number: 345-78-8
Trademarks: Galpseud (Galen); Novafed (HMR); Rhinalair (Fabre); Otrinol (Novartis); Sudafed (Glaxo Wellcome)
Properties: Needles, mp 182.5-183.5°. [a]D20 +62.05°. uv max (ethanol): 208, 251, 257, 264 nm (e 8300, 161, 201, 161). pKa 9.22. Soly at 25° (g/ml): water 2.0; chloroform 0.011; ethanol 0.278. Partition coefficient (25°): 0.010 (n-octanol/water, pH 1.2); 0.049 (n-octanol/water, pH 6.0). LD50 i.p. in mice: 1.0 mmole/kg (Fairchild, Alles).
Melting point: mp 182.5-183.5°
pKa: pKa 9.22
Optical Rotation: [a]D20 +62.05°
Log P: Partition coefficient (25°): 0.010 (n-octanol/water, pH 1.2); 0.049 (n-octanol/water, pH 6.0)
Absorption maximum: uv max (ethanol): 208, 251, 257, 264 nm (e 8300, 161, 201, 161)
Toxicity data: LD50 i.p. in mice: 1.0 mmole/kg (Fairchild, Alles)
 
Derivative Type: Sulfate
CAS Registry Number: 7460-12-0
Trademarks: Afrinol (Schering)
 
Therap-Cat: Decongestant (nasal).
Keywords: Decongestant; a-Adrenergic Agonist.

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